2-(Benzo[d][1,3]dioxol-5-ylamino)-3-hydroxynaphthalene-1,4-dione

ID: ALA4524841

PubChem CID: 155538807

Max Phase: Preclinical

Molecular Formula: C17H11NO5

Molecular Weight: 309.28

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1C(O)=C(Nc2ccc3c(c2)OCO3)C(=O)c2ccccc21

Standard InChI:  InChI=1S/C17H11NO5/c19-15-10-3-1-2-4-11(10)16(20)17(21)14(15)18-9-5-6-12-13(7-9)23-8-22-12/h1-7,18,21H,8H2

Standard InChI Key:  GNKANKXFDWDCFR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    2.8313  -17.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8302  -17.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5448  -18.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5430  -16.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2582  -17.1092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2571  -17.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9699  -18.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6883  -17.9396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6895  -17.1112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9722  -16.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9722  -15.8689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9675  -19.1752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4048  -16.7005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4015  -18.3539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1170  -17.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8273  -18.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8269  -16.7120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1148  -17.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5459  -17.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5396  -17.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3222  -18.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8123  -17.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3325  -16.8762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  7 12  2  0
  9 13  1  0
  8 14  1  0
 14 15  1  0
 15 16  2  0
 16 20  1  0
 19 17  1  0
 17 18  2  0
 18 15  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4524841

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 309.28

Molecular Weight (Monoisotopic): 309.0637

AlogP: 2.68

#Rotatable Bonds: 2

Polar Surface Area: 84.86

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.28

CX Basic pKa: ┄

CX LogP: 1.51

CX LogD: 0.36

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.89

Np Likeness Score: -0.15

References

1. Calil FA, David JS, Chiappetta ERC, Fumagalli F, Mello RB, Leite FHA, Castilho MS, Emery FS, Nonato MC..  (2019)  Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase.,  167  [PMID:30776695] [10.1016/j.ejmech.2019.02.018]

Source

Source(1):

• Scientific Literature